Dimethylamine, hydrochloride → N-[4-[3-(Dimethylamino)propyl]phenyl]acetamide

HRID 2236952Notes

Reaction equation

HRID 2236952 reaction equation
O=[CH:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[CH:7][CH:6]=1.Cl.[CH3:16][NH:17][CH3:18].C([O-])(=O)C.[Na+].C([BH3-])#N.[Na+]>CO>[CH3:16][N:17]([CH3:18])[CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 99206073-(4-Acetamidophenyl)propanal

Product 1

HCID 21685341N-[4-[3-(Dimethylamino)propyl]phenyl]acetamideYield 127.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of N-[4-(3-Oxo-propyl)-phenyl]-acetamide (96 mg, 0.50 mmol), dimethylamine hydrochloride (82 mg, 1.0 mmol), and sodium acetate (66 mg, 0.80 mmol) in methanol (0.5 mL) is added sodium cyanoborohydride (47 mg, 0.75 mmol). Upon completion of the reaction, the solvent is evaporated under reduced pressure and the residue is partitioned between ethyl acetate and water. The aqueous phase is extracted with ethyl acetate. The combined extracts were concentrated to give N-[4-(3-dimethylamino-propyl)-phenyl]-acetamide (0.14 g, >100%).

Workup

  1. customUpon completion of the reaction
  2. customthe solvent is evaporated under reduced pressure
  3. customthe residue is partitioned between ethyl acetate and water
  4. extractionThe aqueous phase is extracted with ethyl acetate
  5. concentrationThe combined extracts were concentrated

Sources & evidence

ORD record
ord-caa2673c1e1949ed8e4a7609b16d0e35
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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